The objective of this proposal is the development of a practical chiral reducing agent (or agents) which will accomplish the conversion of a wide spectrum of prochiral unsaturated compounds (RR'C equals O, RR' equals NR", RR' C equals CR'R") to chiral products with high stereoselectivities. The initial major emphasis will be the conversion of achiral carbonyl compounds to chiral secondary carbinols (and 1- deuterio primary alcohols) with high enantiomeric purity. Such a reagent would obviate the necessity for tedious, time consuming and expensive resolution procedures. Several reagents are contemplated which can be represented by LiA1(OR*)2H2 where OR* represents a chiral ligand attached to the mixed metallo hydride reagent. Two such reagents can be represented by LiA1(OCHRCHROCH3)2H2 and LiA1(OCHRCHRNMe2)2H2. These are analogous to the commercially important achiral sodium bis(2-methoxyethoxy)-aluminum hydride reagent (Red-A1 or Vitride). A systematic investigation of chiral glycols and carbinol-amines as ligands for such a reagent will be made. Emphasis will be placed on testing reagents where there is a diversity in the R groups on the chiral centers (e.g., CF3-, Ph-, PhCH2-, o-anisyl, C6F5-, etc.) and where the R groups are involved in a rigid ring system.